Gaylan Greenawalt
Product management coach for veterans and aspiring product managers
| Hourly rate range | $90 to $175 an hour |
|---|---|
| Focus areas | |
| Works with | Veterans |
| Also coaches | Executive coach |
| Credentials | Bachelor's degree in Quantitative Economics, United States Naval Academy |
Gaylan Greenawalt is a product management coach who helps people break into product roles and grow in them. Gaylan also coaches military and first responder veterans who want to move into tech. Gaylan worked as a product manager at LinkedIn, Amazon, Guideline and Airspeed. Gaylan served 11 years as a Navy officer and led teams of 30 to 100 people across 4 deployments. Gaylan now works as a senior product manager at Overland AI.
What Gaylan helps with
Gaylan helps people move into product management and tech. Gaylan also works on stakeholder management and building systems that scale.
- Breaking into product management
- Moving from the military or first responder work into tech
- Working in B2B SaaS and defense tech
- Chief of Staff roles
- Managing executive stakeholders
- Building team and organization systems that scale
Who Gaylan works with
Gaylan works with military and first responder veterans who want to move into the tech industry. Gaylan also works with people trying to break into product management. Gaylan coaches people aiming for Chief of Staff roles.
Background and qualifications
Gaylan graduated from the United States Naval Academy with a degree in Quantitative Economics. Gaylan served 11 years as a Navy officer. Gaylan led teams of 30 to 100 people through 4 deployments. Gaylan worked as a Navy-Senate liaison and as deputy chief of staff to the Navy's Chief of Legislative Affairs. In tech, Gaylan was a product manager at LinkedIn on Sales Navigator, at Amazon on Kindle Unlimited and Prime Reading, and at Guideline, where Gaylan led a team of 12. Gaylan also worked at Airspeed. Gaylan is now a senior product manager at Overland AI.
Gaylan Greenawalt pricing
Programs and services
- Product management coaching
- Chief of Staff coaching
Gaylan Greenawalt reviews
The CoachVouch take
Gaylan is a Navy veteran who moved into product management at LinkedIn and Amazon, so Gaylan knows the veteran-to-tech path firsthand.
Best for veterans and career changers who want to land a product management or Chief of Staff role in tech.
Common questions
How much does Gaylan Greenawalt charge?
Coaching with Gaylan runs $90 to $175 an hour. Request an intro for an exact quote.
What does Gaylan Greenawalt help with?
Gaylan Greenawalt helps with breaking into product management, moving from the military or first responder work into tech, working in B2B SaaS and defense tech and chief of Staff roles.
Is Gaylan Greenawalt certified?
Gaylan Greenawalt lists: Bachelor's degree in Quantitative Economics, United States Naval Academy.
Does Gaylan Greenawalt coach military veterans?
Yes. Gaylan coaches military and first responder veterans who are moving into the tech industry. Gaylan is a Navy veteran themselves.
How do I contact Gaylan Greenawalt?
Request an intro on this page. It's free, and we'll connect you with Gaylan and, if you want, 2 or 3 similar coaches to compare.
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Last updated September 2026. Request a correction.